N'-(2-Chloro­benzoyl)-N-(pyrrolidin-1-yl)­thio­urea

In the title compound, C₁₂H₁₃ClN₂OS, the mol­ecule has a twisted conformation with regard to the carbonyl and thio­carbonyl groups. In the crystal structure, hydrogen-bonded pairs of mol­ecules are formed which stack along [100].

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.049
• wR factor = 0.107
• Data-to-parameter ratio = 16.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



CELLV_02  Alert C The supplied cell volume s.u. differs from that
          calculated from the cell parameter s.u.'s by > 2
          Calculated cell volume su =      14.42
          Cell volume su given      =      12.00


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

---

Computing details

Data collection: XSCANS (Bruker, 1996); cell refinement: XSCANS; data reduction: SHELXTL (Bruker, 1998); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

N'-(2-Chlorobenzoyl)-N-(pyrrolidin-1-yl)thiourea

Crystal data

C12H13ClN2OS	Z = 2
Mr = 268.75	F(000) = 280
Triclinic, P1	Dx = 1.412 Mg m^−3
a = 7.299 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.039 (1) Å	Cell parameters from 25 reflections
c = 10.096 (1) Å	θ = 7.1–15.9°
α = 67.03 (1)°	µ = 0.45 mm^−1
β = 69.32 (1)°	T = 293 K
γ = 88.43 (1)°	Prism, colourless
V = 631.98 (12) Å^3	0.28 × 0.25 × 0.12 mm

Data collection

Bruker P4 diffractometer	1692 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.023
Graphite monochromator	θmax = 26.4°, θmin = 2.2°
ω scans	h = −1→9
Absorption correction: ψ scan (North et al., 1968)	k = −12→12
Tmin = 0.867, Tmax = 0.947	l = −11→11
3181 measured reflections	3 standard reflections every 397 reflections
2552 independent reflections	intensity decay: <1%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.049	H-atom parameters constrained
wR(F^2) = 0.107	w = 1/[σ^2(Fo^2) + (0.0363P)^2 + 0.1907P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
2552 reflections	Δρmax = 0.28 e Å^−3
155 parameters	Δρmin = −0.29 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.049 (4)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The H atoms were introduced at calculated positions as riding atoms, with bond lengths of 0.86(N—H), 0.93(CH-aromatic), and 0.97(CH₂) Å. The isotropic displacement parameters, U_iso(H), were made equal to = 1.2U_eq(parent atom).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.39682 (13)	0.25002 (11)	1.00157 (10)	0.0649 (3)
S1	0.44259 (12)	0.36357 (8)	0.38561 (9)	0.0437 (2)
O1	0.7075 (3)	0.1040 (2)	0.6929 (3)	0.0551 (6)
N1	0.5182 (3)	0.2874 (2)	0.6433 (3)	0.0344 (6)
H1A	0.4843	0.3642	0.6592	0.041*
N2	0.3313 (3)	0.1124 (2)	0.6317 (3)	0.0375 (6)
C1	0.6417 (4)	0.3265 (3)	0.8918 (3)	0.0408 (7)
C2	0.7294 (5)	0.4102 (3)	0.9388 (4)	0.0534 (9)
H2A	0.6582	0.4254	1.0272	0.064*
C3	0.9232 (6)	0.4711 (4)	0.8538 (4)	0.0578 (9)
H3A	0.9816	0.5313	0.8822	0.069*
C4	1.0311 (5)	0.4432 (4)	0.7267 (4)	0.0558 (9)
H4A	1.1633	0.4820	0.6713	0.067*
C5	0.9427 (4)	0.3576 (3)	0.6818 (4)	0.0442 (8)
H5A	1.0163	0.3385	0.5964	0.053*
C6	0.7460 (4)	0.2999 (3)	0.7620 (3)	0.0341 (6)
C7	0.6550 (4)	0.2174 (3)	0.6996 (3)	0.0354 (6)
C8	0.4279 (4)	0.2444 (3)	0.5614 (3)	0.0328 (6)
C9	0.2289 (5)	0.0538 (3)	0.5592 (4)	0.0460 (8)
H9A	0.3227	0.0427	0.4694	0.055*
H9B	0.1360	0.1176	0.5277	0.055*
C10	0.1226 (5)	−0.0927 (4)	0.6850 (4)	0.0601 (10)
H10A	0.2037	−0.1699	0.6788	0.072*
H10B	−0.0012	−0.1153	0.6780	0.072*
C11	0.0872 (5)	−0.0731 (4)	0.8337 (4)	0.0573 (9)
H11A	−0.0243	−0.0199	0.8567	0.069*
H11B	0.0640	−0.1664	0.9209	0.069*
C12	0.2788 (5)	0.0141 (3)	0.7962 (4)	0.0498 (8)
H12A	0.2596	0.0687	0.8599	0.060*
H12B	0.3797	−0.0488	0.8107	0.060*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0469 (5)	0.0841 (7)	0.0530 (5)	−0.0094 (5)	−0.0019 (4)	−0.0310 (5)
S1	0.0517 (5)	0.0422 (4)	0.0400 (4)	0.0023 (4)	−0.0218 (4)	−0.0150 (3)
O1	0.0494 (14)	0.0498 (13)	0.0901 (18)	0.0203 (11)	−0.0399 (13)	−0.0410 (13)
N1	0.0399 (14)	0.0316 (12)	0.0432 (14)	0.0099 (11)	−0.0236 (12)	−0.0199 (11)
N2	0.0387 (14)	0.0352 (13)	0.0423 (14)	0.0009 (11)	−0.0197 (12)	−0.0150 (11)
C1	0.0387 (17)	0.0429 (16)	0.0384 (16)	0.0020 (14)	−0.0160 (14)	−0.0124 (13)
C2	0.063 (2)	0.060 (2)	0.0463 (19)	0.0030 (18)	−0.0267 (18)	−0.0246 (17)
C3	0.070 (3)	0.055 (2)	0.066 (2)	−0.0018 (19)	−0.044 (2)	−0.0256 (18)
C4	0.0405 (19)	0.062 (2)	0.064 (2)	−0.0054 (16)	−0.0235 (18)	−0.0204 (18)
C5	0.0353 (17)	0.0519 (19)	0.0508 (18)	0.0052 (14)	−0.0178 (15)	−0.0246 (16)
C6	0.0326 (16)	0.0328 (14)	0.0405 (16)	0.0047 (12)	−0.0199 (13)	−0.0130 (12)
C7	0.0304 (16)	0.0372 (16)	0.0384 (16)	0.0041 (13)	−0.0132 (13)	−0.0149 (13)
C8	0.0281 (15)	0.0359 (15)	0.0394 (15)	0.0079 (12)	−0.0133 (13)	−0.0199 (13)
C9	0.0472 (19)	0.0475 (18)	0.056 (2)	0.0051 (15)	−0.0249 (16)	−0.0293 (16)
C10	0.054 (2)	0.048 (2)	0.084 (3)	−0.0025 (17)	−0.029 (2)	−0.0298 (19)
C11	0.047 (2)	0.0474 (19)	0.066 (2)	−0.0070 (16)	−0.0209 (18)	−0.0106 (17)
C12	0.049 (2)	0.0442 (17)	0.0520 (19)	−0.0023 (15)	−0.0232 (16)	−0.0109 (15)

Geometric parameters (Å, º)

Cl1—C1	1.739 (3)	C4—H4A	0.9300
S1—C8	1.676 (3)	C5—C6	1.382 (4)
O1—C7	1.211 (3)	C5—H5A	0.9300
N1—C7	1.366 (3)	C6—C7	1.502 (4)
N1—C8	1.408 (3)	C9—C10	1.513 (4)
N1—H1A	0.8600	C9—H9A	0.9700
N2—C8	1.312 (3)	C9—H9B	0.9700
N2—C12	1.473 (4)	C10—C11	1.521 (5)
N2—C9	1.478 (3)	C10—H10A	0.9700
C1—C2	1.376 (4)	C10—H10B	0.9700
C1—C6	1.388 (4)	C11—C12	1.517 (4)
C2—C3	1.375 (5)	C11—H11A	0.9700
C2—H2A	0.9300	C11—H11B	0.9700
C3—C4	1.379 (5)	C12—H12A	0.9700
C3—H3A	0.9300	C12—H12B	0.9700
C4—C5	1.378 (4)
C7—N1—C8	125.5 (2)	N2—C8—N1	116.7 (2)
C7—N1—H1A	117.2	N2—C8—S1	124.0 (2)
C8—N1—H1A	117.2	N1—C8—S1	119.23 (19)
C8—N2—C12	126.4 (2)	N2—C9—C10	104.3 (2)
C8—N2—C9	122.3 (2)	N2—C9—H9A	110.9
C12—N2—C9	110.4 (2)	C10—C9—H9A	110.9
C2—C1—C6	121.3 (3)	N2—C9—H9B	110.9
C2—C1—Cl1	118.6 (2)	C10—C9—H9B	110.9
C6—C1—Cl1	120.0 (2)	H9A—C9—H9B	108.9
C3—C2—C1	119.4 (3)	C9—C10—C11	103.4 (3)
C3—C2—H2A	120.3	C9—C10—H10A	111.1
C1—C2—H2A	120.3	C11—C10—H10A	111.1
C2—C3—C4	120.2 (3)	C9—C10—H10B	111.1
C2—C3—H3A	119.9	C11—C10—H10B	111.1
C4—C3—H3A	119.9	H10A—C10—H10B	109.1
C5—C4—C3	119.9 (3)	C12—C11—C10	102.6 (3)
C5—C4—H4A	120.1	C12—C11—H11A	111.2
C3—C4—H4A	120.1	C10—C11—H11A	111.2
C4—C5—C6	120.9 (3)	C12—C11—H11B	111.2
C4—C5—H5A	119.6	C10—C11—H11B	111.2
C6—C5—H5A	119.6	H11A—C11—H11B	109.2
C5—C6—C1	118.2 (3)	N2—C12—C11	102.7 (2)
C5—C6—C7	118.1 (3)	N2—C12—H12A	111.2
C1—C6—C7	123.7 (3)	C11—C12—H12A	111.2
O1—C7—N1	124.0 (3)	N2—C12—H12B	111.2
O1—C7—C6	122.5 (3)	C11—C12—H12B	111.2
N1—C7—C6	113.4 (2)	H12A—C12—H12B	109.1
C6—C1—C2—C3	1.2 (5)	C5—C6—C7—N1	−111.3 (3)
Cl1—C1—C2—C3	179.8 (2)	C1—C6—C7—N1	66.0 (3)
C1—C2—C3—C4	−2.9 (5)	C12—N2—C8—N1	11.3 (4)
C2—C3—C4—C5	2.0 (5)	C9—N2—C8—N1	179.7 (2)
C3—C4—C5—C6	0.5 (5)	C12—N2—C8—S1	−166.7 (2)
C4—C5—C6—C1	−2.1 (4)	C9—N2—C8—S1	1.7 (4)
C4—C5—C6—C7	175.4 (3)	C7—N1—C8—N2	57.7 (4)
C2—C1—C6—C5	1.2 (4)	C7—N1—C8—S1	−124.2 (2)
Cl1—C1—C6—C5	−177.3 (2)	C8—N2—C9—C10	−174.5 (3)
C2—C1—C6—C7	−176.1 (3)	C12—N2—C9—C10	−4.4 (3)
Cl1—C1—C6—C7	5.4 (4)	N2—C9—C10—C11	27.6 (3)
C8—N1—C7—O1	−4.2 (4)	C9—C10—C11—C12	−40.2 (3)
C8—N1—C7—C6	171.8 (2)	C8—N2—C12—C11	149.1 (3)
C5—C6—C7—O1	64.8 (4)	C9—N2—C12—C11	−20.5 (3)
C1—C6—C7—O1	−117.9 (3)	C10—C11—C12—N2	36.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···S1^i	0.86	2.63	3.412 (3)	152
C12—H12B···O1	0.97	2.50	2.968 (5)	109

Symmetry code: (i) −x+1, −y+1, −z+1.